Synthesis of Oxylipin Mimics and Their Antifungal Activity against the Citrus Postharvest Pathogens
Nine oxylipin mimics were designed and synthesized starting from d-mannose. Their antifungal activity against three citrus postharvest pathogens was evaluated by spore germination assay. The results indicated that all the compounds significantly inhibited the growth of Penicillium digitatum, Penicil...
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MDPI AG
2016-02-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/21/2/254 |
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| author | Jimei Ma Yupeng Li Hangwei Chen Zhen Zeng Zi-Long Li Hong Jiang |
| author_facet | Jimei Ma Yupeng Li Hangwei Chen Zhen Zeng Zi-Long Li Hong Jiang |
| author_sort | Jimei Ma |
| collection | DOAJ |
| description | Nine oxylipin mimics were designed and synthesized starting from d-mannose. Their antifungal activity against three citrus postharvest pathogens was evaluated by spore germination assay. The results indicated that all the compounds significantly inhibited the growth of Penicillium digitatum, Penicillium italicum and Aspergillus niger. The compound (3Z,6Z,8S,9R,10R)-octadeca-3,6-diene-8,9,10-triol (3) exhibited excellent inhibitory effect on both Penicillium digitatum (IC50 = 34 ppm) and Penicillium italicum (IC50 = 94 ppm). Their in vivo antifungal activities against citrus postharvest blue mold were tested with fruit inoculated with the pathogen Penicillium italicum. The compound (3R,4S)-methyl 3,4-dihydroxy-5-octyltetrahydrofuran-2-carboxylate (9) demonstrated significant efficacy by reducing the disease severity to 60%. The antifungal mechanism of these oxylipin mimics was postulated in which both inhibition of pathogenic mycelium and stimuli of the host oxylipin-mediated defense response played important roles. |
| first_indexed | 2024-04-12T17:11:54Z |
| format | Article |
| id | doaj.art-43d0297304be40a29a12d5a086c0f990 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-12T17:11:54Z |
| publishDate | 2016-02-01 |
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| series | Molecules |
| spelling | doaj.art-43d0297304be40a29a12d5a086c0f9902022-12-22T03:23:46ZengMDPI AGMolecules1420-30492016-02-0121225410.3390/molecules21020254molecules21020254Synthesis of Oxylipin Mimics and Their Antifungal Activity against the Citrus Postharvest PathogensJimei Ma0Yupeng Li1Hangwei Chen2Zhen Zeng3Zi-Long Li4Hong Jiang5Department of Chemistry, College of Sciences, Huazhong Agricultural University, Wuhan 430070, ChinaDepartment of Chemistry, College of Sciences, Huazhong Agricultural University, Wuhan 430070, ChinaDepartment of Chemistry, College of Sciences, Huazhong Agricultural University, Wuhan 430070, ChinaDepartment of Chemistry, College of Sciences, Huazhong Agricultural University, Wuhan 430070, ChinaDepartment of Chemistry, College of Sciences, Huazhong Agricultural University, Wuhan 430070, ChinaDepartment of Chemistry, College of Sciences, Huazhong Agricultural University, Wuhan 430070, ChinaNine oxylipin mimics were designed and synthesized starting from d-mannose. Their antifungal activity against three citrus postharvest pathogens was evaluated by spore germination assay. The results indicated that all the compounds significantly inhibited the growth of Penicillium digitatum, Penicillium italicum and Aspergillus niger. The compound (3Z,6Z,8S,9R,10R)-octadeca-3,6-diene-8,9,10-triol (3) exhibited excellent inhibitory effect on both Penicillium digitatum (IC50 = 34 ppm) and Penicillium italicum (IC50 = 94 ppm). Their in vivo antifungal activities against citrus postharvest blue mold were tested with fruit inoculated with the pathogen Penicillium italicum. The compound (3R,4S)-methyl 3,4-dihydroxy-5-octyltetrahydrofuran-2-carboxylate (9) demonstrated significant efficacy by reducing the disease severity to 60%. The antifungal mechanism of these oxylipin mimics was postulated in which both inhibition of pathogenic mycelium and stimuli of the host oxylipin-mediated defense response played important roles.http://www.mdpi.com/1420-3049/21/2/254oxylipinsynthesisantifungal activitycitruspathogen |
| spellingShingle | Jimei Ma Yupeng Li Hangwei Chen Zhen Zeng Zi-Long Li Hong Jiang Synthesis of Oxylipin Mimics and Their Antifungal Activity against the Citrus Postharvest Pathogens Molecules oxylipin synthesis antifungal activity citrus pathogen |
| title | Synthesis of Oxylipin Mimics and Their Antifungal Activity against the Citrus Postharvest Pathogens |
| title_full | Synthesis of Oxylipin Mimics and Their Antifungal Activity against the Citrus Postharvest Pathogens |
| title_fullStr | Synthesis of Oxylipin Mimics and Their Antifungal Activity against the Citrus Postharvest Pathogens |
| title_full_unstemmed | Synthesis of Oxylipin Mimics and Their Antifungal Activity against the Citrus Postharvest Pathogens |
| title_short | Synthesis of Oxylipin Mimics and Their Antifungal Activity against the Citrus Postharvest Pathogens |
| title_sort | synthesis of oxylipin mimics and their antifungal activity against the citrus postharvest pathogens |
| topic | oxylipin synthesis antifungal activity citrus pathogen |
| url | http://www.mdpi.com/1420-3049/21/2/254 |
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